2‐Thioxo‐1,3‐thiazepan‐4‐ones, a novel class of cyclic dithiourethanes with a 7‐membered ring system | Zendy

Hanefeld Wolfgang | Zendy; Schütz Harald | Zendy

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2‐Thioxo‐1,3‐thiazepan‐4‐ones, a novel class of cyclic dithiourethanes with a 7‐membered ring system

Author(s) -

Hanefeld Wolfgang,

Schütz Harald

Publication year - 1999

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570360509

Subject(s) - chemistry , ring (chemistry) , butyric acid , isothiocyanate , medicinal chemistry , cyclic amines , stereochemistry , organic chemistry , catalysis

Reaction of isothiocyanates 1 with γ‐thiobutyrolactone ( 2 ) in alkaline medium yielded 4‐thiocarbamoylthiobutyric acids 3 after acidification, which could be cyclized to the 2‐thioxo‐1,3‐thiazepan‐4‐ones 6 . Additional reactions were observed with the formation of 6t from p ‐phenylenediisothiocyanate ( 1s ) and with the formation of 6w from benzyl isothiocyanate ( 1t ). 3‐Acetylamino‐γ‐thiobutyrolactone ( 7 ) could also be used in this reaction yielding the butyric acid derivatives 3u‐3w . Cyclization yielded the 1,3‐thiazepane derivatives 6x, y which rearranged under ring contraction to the 1,3‐thiazinanes 8a, b .

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